‘Gambling Man’: Masayoshi Son’s Wild Ride – Book and Film Globe

Lionel Barber, a former editor of the Financial Times, has written a book that will stoke admiration for SoftBank CEO Masayoshi Son even as it gives ammunition to his critics.

The figure at the center of Gambling Man: The Secret Story of Japan’s Masayoshi Son has displayed many of the noblest, along with some of the most self-destructive, tendencies in venture capitalism.

To illustrate this paradox, it helps to contrast one of the biggest startup successes of all time, China’s tech giant Alibaba, with the now bankrupt office-space leasing app WeWork. Son, the grandchild of a Korean immigrant who came to Japan in 1917 to work in the coal mines, studied at Berkeley before commencing his rise through the worlds of finance and investing and becoming CEO of SoftBank. As Barber details, Son went out on a limb for companies that had potential but also those with illusory promise. He picked winners as well as losers.

With hindsight, Alibaba stands out as maybe the canniest investment that Son could have made, while WeWork seems an instance of poor judgment. Barber does not blame Son for proving vulnerable to the charms of WeWork founder Adam Neumann, who comes across here as a bright, savvy young entrepreneur. Yet Barber is blunt about the myopic mindset that he argues failed to identify meaningful differences between WeWork and other companies in an industry that met with cratering demand in the global pandemic.

At the end of the day, SoftBank lost $14 billion on its WeWork investment. Meanwhile, lots of startups that had sound models and abundant talent went ignored.

As Barber makes clear, part of the issue here is that angel investors and venture capitalists do not rest on their laurels. The pressure to be the force behind the next big thing is immense, and does not let up.

As the reader grows engrossed in this narrative, it is hard not to admire Son’s unbridled, often reckless ambition, to wish for his schemes to succeed, or to share his frustration when they hit a wall. For years, Son pushed the merger of his portfolio company Sprint with T-Mobile, only for President Barack Obama’s antitrust regulators to scupper the deal. With the election of another bold entrepreneur, not known for thinking small, as president of the United States, Son finally got to see the merger come to fruition on April 1, 2020, even if T-Mobile then amalgamated Sprint and made a memory of it.

Having chosen to write a work of popular business journalism, Barber does not devote much time to algorithms or formulae driving SoftBank’s far-flung investments. Son is a maverick who will take chances on deals others find too iffy to touch. Though he admires Steve Jobs, not everything he chooses to invest in has to be the next Apple. Tech gurus, startup founders, and Saudi royalty are far from the only characters in the rogues’ gallery of partners and visionaries that fills this book.

Son came to the rescue of none other than Kevin Costner when the Dances With Wolves star had fallen out of favor with some of the tribes in the Black Hills of South Dakota and needed an angel to help him acquire 630 acres of federal land next to the casino that Costner named after his character in that film. No doubt there were potentially more lucrative investment targets out there, but that did not stop Son from throwing the might of SoftBank behind the actor.

“As an investor, Masa often operated on little more than a whim,” Barber writes.

Here was both a blessing and a curse. It drew, and continues to draw, plenty of admiration for Son, but has also made him a pariah for people who forget the biblical injunction about letting whoever is without sin cast the first stone.

After the Wall Street Journal published an exposé in September 2019 suggesting that WeWork founder Neumann lived extravagantly, and detailing allegations about the discovery of drugs on Neumann’s flights to and from Israel, one of the harshest reactions, in Barber’s telling, came from Larry Fink, the CEO of the world’s largest asset manager, BlackRock.

“Larry Fink, who had engaged in a fireside chat about good governance and high-tech investing with Masa the previous evening, was appalled. WeWork, he told friends, was uninvestable,” writes Barber.

The man who called WeWork uninvestable on the grounds of Neumann’s supposed libertinism happens to be the CEO of an asset manager that just last year bought a majority share in a facility off Italy’s coast processing carbon-intensive liquid natural gas, and that has long been bullish on China. So much so, in fact, that it received a letter from the U.S. House Select Committee on the Chinese Communist Party, whose members had concerns that investments in China’s state-owned entities would benefit the regime’s military and spy agencies and help its extensively documented use of slave labor and genocide against the Uyghurs of Xinjiang province.

Alibaba, to its credit, is often at odds with Beijing’s regulators. It is a tragedy that WeWork fell apart, but Son’s aim here was to support a company that made use of up-to-the-minute technologies to offer entrepreneurs something they wanted and remove a few of the headaches from office expansions.

In the final passages of Gambling Man, Barber presents far more substantive grounds for treating Masayoshi Son with caution. In these pages, Son comes across as a huge believer in artificial intelligence and what he sees as its ability to remake human existence, not just through labor-saving tweaks here and there, but in ways so radical that most people even now have no inkling of them. Having taken a beating in one financial crisis, setback, and failed investment after another, Son has emerged as one of the most passionate backers of AI and takes pride in his friendship with Sam Altman.

But given how little idea we, by Son’s own eager admission, have of what AI means for our future and how much autonomy it will leave people in their personal and professional lives, this zeal may strike readers as by far the most ill-advised gamble in the book.